While he [Matt Groening] is “flattered” by the street response to “The Simpsons,” “I must say I have mixed feelings. You have to have mixed feelings when you’re getting ripped off,” Groening says.
– The Washington Post, 6/28/90

It was more than just a bootleg. Combining hip hop culture references with hand-drawn illustrations, black Bart Simpson t-shirts were an underground phenomenon in the late 80s and early 90s. A cultural meme before the internet even existed.

Not only did the shirts look cool, but they carried a whiff of black market cache. It was the opposite of rocking a label. Black Bart didn’t mean that you had money, but he meant you were in-the-know.

The shirts were hawked in concert parking lots, hung in boardwalk tourist traps, laid out on folding tables in the Fulton Mall, and crowded into Chinatown’s fake-rolex shops. They were sold in the small, unregulated economies between the cracks of the American retail landscape. There was no headquarters to shut down. The shirts were produced and distributed through a network of independent hustlers and small fries operating concurrently.

Matt Groening couldn’t stop it. 20th Century Fox couldn’t stop it. Black Bart shirts stopped because they belonged to hip hop subculture. When they entered the mainstream, their cred burned up in the light and production got big enough to shut down.

This is my undisputed Shangri-La of bootleg Bart shirts. The MC Hammer/Jordan Flight mash-up and the composition is so fresh. Can’t touch this!